


Pretty in Pink

by AnnaNocturnal



Series: Requests and Challenges [2]
Category: Supernatural
Genre: Feminization, M/M, Panty Kink, Situational Humiliation, Supernatural Kink Meme, Verbal Humiliation
Language: English
Status: Completed
Published: 2015-04-04
Updated: 2015-04-04
Packaged: 2018-03-21 04:42:19
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,629
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3677946
Author URL: https://archiveofourown.org/users/AnnaNocturnal/pseuds/AnnaNocturnal
Summary: <blockquote class="userstuff">
              <p>Dean's always had a thing for pretty pink panties. He can't even begin to imagine what would happen if Sam found out...</p>
            </blockquote>





	Pretty in Pink

**Author's Note:**

> Written for [this prompt](http://spnkink-meme.livejournal.com/94674.html?thread=37002194#t37002194) at the spnkink-meme livejournal community.

Every man has that one woman in his past who he may not still be with, may not even _want_ to be with, but who changed him in strange and permanent ways during his time with her. For Stanley it was Stella, for John it was Yoko, for Sid it was Nancy, for Ozzie it was Harriet. As for Dean, well… For Dean Winchester, that woman was Rhonda Hurley.

Dean hadn’t known Rhonda for very long, in the grand scheme of things. He had been seventeen when he and the other two Winchesters blew through Kittery Point, Maine, where John had left them as he hunted a few things in the surrounding area. They were there a month, tops. But even after all Dean had seen since, he still looked back on that time as perhaps the most surreal month of his life. It had passed by quickly and crawled at a snails pace all at the same time. All because of Rhonda Hurley.

The things they did ranged from as vanilla as it gets—sloppy makeouts and missionary-style on the couch in the finished basement of her parents house—to absolutely deviant and terrifying—Dean cuffed to the headboard of her father’s bed as she ate his ass, refusing to unlock the cuffs until he came from that alone, his mind too gone to pick them, as the sound of the garage door opening heralded her father’s arrival home.

He had learned a lot from Rhonda Hurley.

But one thing, above all, stuck with him even now, fifteen years later. One itch that he couldn’t seem to completely satisfy once and for all.

Those pink lacy panties.

Dean had three pair, tucked into a discreet pocket on the inside of his duffel bag. It made him side-eye Sam when he went into his brother’s bag for anything with such hostility that Sam eventually just accepted that they had a don’t-touch-each-other’s-stuff policy of some sort. Which was just fine with Dean. He could think of only one passable excuse for there to be panties in his duffel bag that _didn’t_ involve him wearing them himself, and he somehow thought that it would actually be worse in the long run to claim that they were trophies from women he had bedded, considering he and Sam had been involved for over a year now.

Best to just keep it quiet.

But since he and Sam had started fucking around—or whatever they were doing—Dean had less and less opportunity to indulge in the soft, tantalizing feel of the lace and silk against his most sensitive spots. It was hard to be comfortable wearing them under his clothes in secret, knowing that at any moment his little brother may decide to bend him over in whatever hotel room they were occupying and pull his pants down to fuck him.

Dean felt his face flame any time he imagined the look on Sam’s face if he were to pull his pants down to find the delicate pink fabric (barely) covering his ass.

So he had taken to sneaking around, as though the panties were his mistress, slipping them on any time Sam left him on his own for a period of time. By the time Sam returned—bless his little brother for always being so exact and punctual—the panties were always tucked back in the pocket of his duffel, his normal boxer briefs in place once more under his jeans.

And if Dean was a little more aggressive and in need of release when his little brother returned, he certainly wasn’t hearing any complaints.

He probably should’ve figured that it was working too well, that it would fall apart eventually.

They were working a case in upstate Michigan when that ill-fated day arrived. No idea yet _what_ they were hunting; only that it was a nasty sonuvabitch that seemed to have a taste for young virgins. Dean was hedging his bets on a pagan god. Sam had contacted some scholar he knew of at some university and was planning to go meet with him that evening, see if he could make sense of any of the evidence they had gathered so far.

When Dean heard that Sam expected to be gone at least two hours, including travel time, he was instantly half-hard. It took everything in him to keep his voice calm and steady, his movements normal and fluid, and _not_ shove Sam out the door when it came time for him to leave.

Dean waited until he heard the Impala leave the parking lot before crossing the room to his duffle bag, shoving jeans and henleys to the side to get to the zippered pocket. He paused, his heart thudding, ears piqued for any noise when his fingers closed around the delicate fabric. Once he was sure that he couldn’t hear the Impala signaling an unexpected return by Sam, Dean brought out the pair in his hand, a pair of cheeky-cut (which Rhonda Hurley had explained minimized panty lines; like _that_ was Dean’s concern) light pink ones, all sheer, silky lace, with a tiny pink bow on the waistband.

He ran his fingers over the fabric, teasing himself with the thought of what they were going to feel like when he slid them on, the smooth fabric rubbing against his dick and balls, cupping them tight as his dick, too big to be completely restrained by the delicate lace, leaked on his stomach.

The thought made his dick throb; he was completely hard and he hadn’t even put them on yet. He set them down on the bed, his eyes trained on them as he undid the button and zipper on his jeans, taking his time, teasing himself. He slipped the jeans and boxer briefs from his hips, freeing his erection, and hissed as it bobbed in the cool air. He resisted the urge to grasp his dick, to run his hand up and down the length, flexing his fingers for a moment before he picked up the panties and slipped them on, sighing as the cool fabric whispered over his skin, setting his nerves on edge.

“ _Fuck_ ,” he sighed, running his fingers over the thin material, ghosting them over the underside of his cock, straining against the front.

He sat on the bed, puling himself back to sit against the headboard and splaying his legs. He felt the lace shift against his balls, the slight scraping sensation against the fine scattered hair combining with the slip-slide of lace causing him to throw his head back and gasp. One hand came down to cup his balls, the other running along the underside of his dick outside of the panties.

He let his mind wander in the blissful fog, conjuring up a fantasy to go with the sensations. For a long time it had been Rhonda, since she had been the only one to ever see him like this, but lately… He imagined Sam walking through the door. He would stop in his tracks when his eyes fell on Dean, the hazel rings disappearing quickly as his pupils dilated. Dean would flush, embarrassed at being caught, but too deep in the pleasure to stop. It would take Sammy a minute to recover; his brother ran hot and cold—sex god or blushing virgin, never anywhere in between. But once he recovered himself he would cross the room, that predatory glint in his eyes as he climbed onto the bed, crawling towards Dean and forcing his hand out of the way. He’d take in the sight of Dean’s weeping cock, the precum smearing against his stomach where his dick was held against his abdomen by the lace.

“ _God, Dean_ ,” Sam would mutter on an exhale, his head dipping down to nose at the fabric stretched over his brother’s impressive dick, inhaling deeply, taking in Dean’s scent.

“ _God, Dean_.” Dean frowned, because he was ninety-percent sure that _that one_ wasn’t in his head. His heartbeat ratcheted up and his eyes flew open. Sure enough, Sam was standing at the door to the hotel room, his mouth hanging open in shock. Dean let out a less-than-manly yelp, his hands moving to cover himself as well as he could.

“Sammy,” he choked out, his face burning with shame. “When…I didn’t hear the Impala.”

“Yeah, it broke down; I had to walk back. Luckily I hadn’t gotten far…” Sam was staring at Dean’s covered package, his eyes dark.

Dean swallowed hard at the predatory look in Sam’s eyes. Then it clicked. “Wait. You left _my baby_ on the side of the road??” He jumped up, heading for the door without further thought.

Sam slammed the door shut and leaned back against it, creating a wall with his body as he slipped his hands casually into his pockets and smirked. “You gonna go get your car, Dean?” He rolled his eyes when Dean looked like he had to be out of his mind to even ask. “You’re gonna march out there and walk a quarter of a mile in your _pretty pink panties_?”

“I…” Dean flushed again, and to his horror he felt tears of embarrassment begin to build at the back of his eyes. He brought his hands forward to shield himself again, his stomach twisting at the idea that Sam was _really_ seeing him like this. Because there was no way in hell that Sam was really going to react the way that dream Sam had.

“Dean, what—” Sam sounded alarmed.

Sam tried to meet his big brother’s eyes but Dean dodged every attempt before turning and heading back towards the bed to pick up his pants off of the floor. He had to bend over to do it, and he thought there was no way that he could feel more ashamed than when he was forced to put his ass on display in those panties.

“Dean, wait!” Sam’s hand closed around his arm, stopping him just before he made it to the bathroom. “Dean, what’s wrong?”

“Didn’t…uh…” Dean shook his head. “Didn’t exactly mean for you to find out about this, Sammy. A little embarrassed, is all.” He let out a harsh laugh. “You probably think I’m some sort of freak.”

Sam was silent and perfectly still for half a beat, and then Dean was being pushed toward the bed until the back of his knees hit the edge, his legs buckling and forcing him to fall to the mattress. Sam was grinning down at him, his tongue flicking out to moisten his lips.

“Yeah, you’re a freak, Dean.” Sam got to his knees slowly, his chest pressed against the mattress between Dean’s knees. His hands rubbed up and down the older man’s thighs, fingertips barely grazing the lace edge of the panties as his eyes devoured his brother. “But it’s _so fucking hot_. Guess that makes me a freak, too.”

“Well, we always knew you were a freak, Sammy.” Dean hadn’t managed to quite wrap his head around this change in events yet, but knowing that Sammy wasn’t mad, wasn’t disgusted, had him laid out, spread out for his brother’s eyes while wearing those fucking panties… Well, that was all Dean needed to understand.

“You were keeping this a secret from me, Dean?” Sam’s voice sounded disapproving. “Sneaking around, waiting for me to leave, keeping this all to yourself?” He leaned down, his lips ghosting over the inside of his brother’s thigh before he bared his teeth and bit down, just hard enough to cause Dean to let out a startled cry. “How long?”

“Fuck, Sammy…” Dean arched his back, one arm tossed over his eyes, unable to meet his brother’s gaze.

“How long?” Sam demanded quietly, his words muffled against the smooth skin of Dean’s thigh.

“Since I was in high school, Sammy.” The words came out in a rush and Dean’s face flamed again.

“That long…” Sam’s fingers ran up the underside of Dean’s dick and he smirked when he felt it throb before wrapping his hand around it, squeezing it through the lace. “What do you think about, Dean?”

“What?” Dean was having trouble forming a clear thought.

Sam chuckled darkly, stroking Dean teasingly, causing the older man to arch into his hand. “You think about being taken? Overpowered? You want someone to see you in your pretty pink panties and fuck you like you’re their bitch? Fuck your tight, needy hole like it’s a pussy?”

“ _Sam_.” Dean had never imagined the effect that hearing his little brother comparing him to a woman would have on him. Never once thought it would make him harder, make him want _that_ , want everything little Sammy was saying.

His brother leaned forward and buried his face in Dean’s crotch, rubbing his cheek and nose against the lace, five o’clock shadow snagging at the fabric. He inhaled deeply, taking in the musky scent. “Gonna fuck you, Dean. Gonna fuck that tight little pussy.” He chuckled as Dean bucked toward him, bringing his hands up to hold his big brother’s hips still. “But first, I’m gonna taste you.”

And before Dean could respond, before he could even process the words his little brother had spoken, his dick was covered in wet heat as Sam’s tongue laved at him through his panties. He cried out, his hands coming to tangle in Sam’s long, thick locks. He tried to thrust up but Sam continued to hold him still, running his tongue over the lace, mouthing him and pressing open-mouthed kisses to his dick.

Dean was dripping precum steadily now and he nearly lost it when Sam’s head moved up to swirl his tongue around the tip, gathering up the bitter liquid. He wasn’t going to last long, the heat of Sam’s mouth and the teasing torture of the lace rubbing against him building steadily into _too much, way too much, too good_. “Can’t take much more, Sammy.”

He felt Sam smile against his dick, felt the tell-tale rhythmic motion of Sam rutting against the side of the mattress. God, his baby brother was getting off on doing this to him, seeing him like this.

“Wanna see you come, Dean. Want you to cover these panties in cum, make them as filthy as you.” Sam moved down to nose at Dean’s balls before taking them into his mouth, sucking lightly through the fabric, soaking the lace and sending Dean’s eyes rolling back in his head at the sensation. “Then I’m gonna strip them off of you, covered in your cum, and make you suck them clean as I fuck your tight, hot pussy.” Sam’s hand moved to press two fingers against Dean’s hole, rubbing the lace against the sensitive skin as though to punctuate his point.

Dean let out a strangled yell, a string of profanities that ended in a broken, “ _Sammy_ ,” and shot his load, his seed spurting against the lace and his stomach as Sam continued to lave at his balls. His eyes started to droop as he came down from his high and he whimpered as Sam continued to suck at his over-sensitive skin.

Finally, Sam pulled away, climbing up over him on the bed to bring their faces close together.

“So fucking hot, Dean,” he muttered, nipping at his jaw and neck. “Don’t go to sleep on me. Still need to fuck that pussy.”

Dean grinned and pulled his brother towards him by the collar of his shirt to press their lips together in a quick, hungry kiss. “Do it, baby boy,” he growled, a challenge lacing his voice as he reveled in the way his little brother’s eyes darkened at the pet name.

Fuck, he should’ve shown Sam his panties a long time ago.

  
**The End.** _I hope you enjoyed it. :)_  



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